Methyl Isocyanate → HCID 67606947, compound

HRID 1965220Notes

Reaction equation

HRID 1965220 reaction equation
[C:1]([O:5][C:6](=[O:39])[N:7]([CH:9]([C:11](=[O:38])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[NH:25][CH2:26][CH:27]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:40][N:41]=[C:42]=[O:43]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:39])[N:7]([CH:9]([C:11](=[O:38])[NH:12][CH:13]([C:18]([N:20]1[CH2:24][CH2:23][CH:22]2[N:25]([C:42](=[O:43])[NH:41][CH3:40])[CH2:26][CH:27]([CH2:28][O:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=3)[CH:21]12)=[O:19])[C:14]([CH3:16])([CH3:17])[CH3:15])[CH3:10])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 67606764HCID 67606764, compound

Product 1

HCID 67606947HCID 67606947, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of amine 84 (220 mg, 0.4 mmol) in DCM (10 mL) was treated with TEA (0.11 mL, 0.78 mmol) followed by methyl isocyanate (0.05 mL, 0.78 mmol). After 2.5 h, the reaction mixture was quenched with MeOH (5 mL) followed by NH4OH (15M, 10 drops). After 10 min, the solution was diluted with DCM, washed successively with 1M HCl, saturated aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 90 as a pale, yellow-colored foam (175 mg, 72%) that was used without further purification. 1H NMR (CDCl3, 300 MHz): δ7.05 (q, J=9.0, 18.3 Hz, 1H), 6.89 (br s, 1H), 6.74-6.67 (m, 1H), 6.60-6.54 (m, 1H), 4.68 (br s, 1H), 4.61 (d, J=9.3 Hz, 1H), 4.51-4.48 (m, 1H), 4.40 (d, J=6.0 Hz, 1H), 4.25-4.22 (m, 1H), 4.08-3.99 (m, 2H), 3.79 (t, J=9.0 Hz, 1H), 3.58-3.55 (m, 1H), 3.47-3.34 (m, 2H), 2.84-2.79 (m, 7H), 2.42-2.36 (m, 1H), 2.13-2.00 (m, 1H), 1.70 (br s, 1H), 1.49 (s, 9H), 1.32 (d, J=6.9 Hz, 3H), 0.98 (s, 9H) ppm.

Workup

  1. customthe reaction mixture was quenched with MeOH (5 mL)
  2. waitAfter 10 min
  3. additionthe solution was diluted with DCM
  4. washwashed successively with 1M HCl, saturated aqueous NaHCO3, and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5c39964fa1124f3089b5905732897663
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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